If you upgrade web2py to the latest and you continue to use python 2.7 everything should work as expected. We do continue to promise python 2.7 backward compatibility (and this is all that we promised).
If you chose to upgrade to python 3.7 than your app will probably no longer work. You will have to convert them from python 2.7 to 3.7. This is not web2py specific. We do not require that you do that. Yet the Python language developer have made the choice of no longer supporting python 2.7 and therefore you should upgrade.
All we offer is, 1) if you port your apps, web2py will still work with them. 2) we offer py4web as a framework build specifically for python 3.7 which supports a lot of the same APIs and is faster.